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Enantioselective Total Synthesis of (–)-Myrifabral A and B

Fulton, Tyler J. and Chen, Anthony Y. and Bartberger, Michael D. and Stoltz, Brian M. (2020) Enantioselective Total Synthesis of (–)-Myrifabral A and B. Chemical Science, 11 (39). pp. 10802-10806. ISSN 2041-6520. https://resolver.caltech.edu/CaltechAUTHORS:20200304-153439734

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Abstract

A catalytic enantioselective approach to the Myrioneuron alkaloids (−)-myrifabral A and (−)-myrifabral B is described. The synthesis was enabled by a palladium-catalyzed enantioselective allylic alkylation, that generates the C(10) all-carbon quaternary center. A key N-acyl iminium ion cyclization forged the cyclohexane fused tricyclic core, while vinyl boronate cross metathesis and oxidation afforded the lactol ring of (−)-myrifabral A. Adaptation of previously reported conditions allowed for the conversion of (−)-myrifabral A to (−)-myrifabral B.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1039/d0sc01141jDOIArticle
http://www.rsc.org/suppdata/d0/sc/d0sc01141j/d0sc01141j1.pdfPublisherSupplementary Information
https://doi.org/10.26434/chemrxiv.11900331.v1DOIDiscussion Paper
ORCID:
AuthorORCID
Fulton, Tyler J.0000-0002-9343-2456
Chen, Anthony Y.0000-0002-9578-4893
Bartberger, Michael D.0000-0002-5167-3139
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2020 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. All publication charges for this article have been paid for by the Royal Society of Chemistry. Submitted 26 Feb 2020; Accepted 20 Apr 2020; First published 21 Apr 2020. We thank NIH-NIGMS (R01GM080269) and Caltech for financial support. Dr Scott Virgil (Caltech) is thanked for instrumentation and SFC assistance. We thank Dr David Vander Velde (Caltech) for NMR expertise, and Dr Mona Shahgholi (Caltech) and Naseem Torian (Caltech) for mass spectrometry assistance. There are no conflicts to declare.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
CaltechUNSPECIFIED
Subject Keywords:myrifabral; myrioneuron; Alkaloids; total synthesis; allylic alkylation
Issue or Number:39
Record Number:CaltechAUTHORS:20200304-153439734
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20200304-153439734
Official Citation:Enantioselective Total Synthesis of (–)-Myrifabral A and B. Chem. Sci., 2020, 11, 10802-10806; doi: 10.1039/d0sc01141j
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:101714
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:04 Mar 2020 23:45
Last Modified:14 Oct 2020 21:26

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